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1,2-Dichloroethane → 2-Chloro-6-{[3-(2-pyridinyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]carbonyl}benzonitrile

HRID 1889118
Notes
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Reaction equation

HRID 1889118 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:25]2[CH2:26][CH2:27][NH:28][CH2:29][C:24]2=[N:23][N:22]=1.[Cl:30][C:31]1[C:32]([C:40]#[N:41])=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=[O:35]>ClCCl.CN(C)C=O>[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:33]([C:34]([N:28]2[CH2:27][CH2:26][N:25]3[C:21]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=4)=[N:22][N:23]=[C:24]3[CH2:29]2)=[O:35])[C:32]=1[C:40]#[N:41]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 523636372-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-3-yl}pyridineHCID 533972953-Chloro-2-cyanobenzoic acid

Product 1

HCID 665992832-Chloro-6-{[3-(2-pyridinyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]carbonyl}benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Procedure

EDC (174 mg, 0.909 mmol) followed by HOBT (127 mg, 0.826 mmol) was added to a suspension of 3-(2-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (I101) (166 mg, 0.826 mmol) and 3-chloro-2-cyanobenzoic acid (I125) (150 mg, 0.826 mmol) in Dichloromethane (DCM) (4 mL) and N,N-dimethylformamide (DMF) (1 mL) and the reaction was stirred at room temperature for 18 h. LCMS indicated that the major peak was the desired product. The solvent was evaporated and the residue partitioned between EtOAc and sat. NaHCO3 and the organic layer was collected. This was dried (Na2SO4) and the solvent evaporated to afford an orange oil. This was purified by MDAP to afford a pale yellow oil which solidified on standing to afford 174 mg of desired product.

Sources & evidence

ORD record
ord-8d549b8776e64de6a914328cdf3aa605
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501946B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes